(1H-1,3-Benzimidazole-5,6-dicarboxylic acid)(5-carboxyl-ato-1H-1,3-benzimidazole-6-carboxylic acid)silver(I) monohydrate.

The title compound, [Ag(C(9)H(5)N(2)O(4))(C(9)H(6)N(2)O(4))]·H(2)O, contains one independent Ag atom, a neutral 1H-benzimidazole-5,6-dicarboxylic acid (bdcH), its monodeprotonated form, i.e. 5-carboxyl-ato-1H-1,3-benzimidazole-6-carboxylic acid (bdc), and one solvent water mol-ecule, the latter being disordered over three sites with site occupancy factors of 0.375 (× 2) and 0.25. In addition, the H atom on one carboxylic acid residue is disordered, being connected to each of the O atoms 50% of the time. The Ag atom is in a virtually linear geometry defined by two N atoms derived from the bdc and bdcH ligands. The three-dimensional supra-molecular structure is stablized by extensive O-H⋯O and N-H⋯O hydrogen bonds. An intramolecular O-H⋯O hydrogen bond is also present.

Related literature

For related structures, see: Gao et al. (2008 ▶); Li et al. (2009 ▶); Lo et al. (2007 ▶); Wei et al. (2008 ▶); Yao et al. (2008 ▶).

Experimental

Crystal data

[Ag(C9H5N2O4)(C9H6N4O2)]·H2O

M = 537.37

Monoclinic,

a = 28.483 (3) Å

b = 18.6398 (17) Å

c = 7.2251 (7) Å

β = 99.046 (1)°

V = 3788.2 (6) Å3

Z = 8

Mo Kα radiation

μ = 1.13 mm−1

T = 298 K

0.31 × 0.23 × 0.19 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.740, T max = 0.807

10329 measured reflections

3675 independent reflections

2572 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.092

S = 1.04

3675 reflections

307 parameters

18 restraints

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.59 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809044535/tk2558sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044535/tk2558Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ag(C9H5N2O4)(C9H6N2O4)]·H2O	F(000) = 2145.0
Mr = 537.37	Dx = 1.885 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2071 reflections
a = 28.483 (3) Å	θ = 2.4–22.4°
b = 18.6398 (17) Å	µ = 1.13 mm−1
c = 7.2251 (7) Å	T = 298 K
β = 99.046 (1)°	Block, colourless
V = 3788.2 (6) Å3	0.31 × 0.23 × 0.19 mm
Z = 8

Bruker APEXII area-detector diffractometer	3675 independent reflections
Radiation source: fine-focus sealed tube	2572 reflections with I > 2σ(I)
graphite	Rint = 0.044
φ and ω scans	θmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −35→35
Tmin = 0.740, Tmax = 0.807	k = −20→22
10329 measured reflections	l = −8→7

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.04P)2] where P = (Fo2 + 2Fc2)/3
3675 reflections	(Δ/σ)max = 0.001
307 parameters	Δρmax = 0.52 e Å−3
18 restraints	Δρmin = −0.59 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ag1	0.374338 (11)	0.168833 (16)	0.58373 (5)	0.04290 (14)
O1	0.36561 (10)	−0.26003 (15)	0.5821 (5)	0.0606 (10)
H1	0.3710	−0.3049	0.5832	0.073*
O2	0.44076 (10)	−0.23159 (15)	0.5698 (5)	0.0547 (9)
O3	0.45996 (10)	−0.11508 (16)	0.3045 (4)	0.0470 (8)
H3	0.4863	−0.1056	0.2688	0.056*	0.50
O4	0.50175 (10)	−0.08915 (16)	0.5782 (4)	0.0491 (8)
H4	0.5006	−0.0830	0.6940	0.059*	0.50
O5	0.30757 (10)	0.53188 (16)	0.6824 (5)	0.0548 (9)
O6	0.28554 (11)	0.42025 (16)	0.6978 (5)	0.0580 (10)
O7	0.37366 (11)	0.60136 (15)	0.6187 (5)	0.0538 (9)
H7	0.3493	0.5781	0.6386	0.065*
O8	0.44651 (11)	0.58811 (16)	0.5706 (5)	0.0612 (10)
N1	0.33935 (11)	0.07120 (16)	0.6181 (5)	0.0314 (8)
N2	0.28969 (11)	−0.01398 (17)	0.6799 (5)	0.0338 (8)
H2A	0.2646	−0.0338	0.7095	0.041*
N3	0.41656 (11)	0.25914 (16)	0.5533 (5)	0.0384 (9)
N4	0.47918 (11)	0.32435 (17)	0.5099 (5)	0.0395 (9)
H4A	0.5071	0.3347	0.4871	0.047*
C1	0.29744 (13)	0.0560 (2)	0.6672 (6)	0.0354 (10)
H1A	0.2757	0.0908	0.6905	0.043*
C2	0.32928 (12)	−0.0490 (2)	0.6369 (6)	0.0287 (9)
C3	0.36007 (13)	0.00500 (19)	0.5978 (6)	0.0275 (9)
C4	0.40427 (13)	−0.01206 (19)	0.5503 (6)	0.0288 (9)
H4B	0.4251	0.0237	0.5247	0.035*
C5	0.41601 (13)	−0.0831 (2)	0.5424 (6)	0.0301 (9)
C6	0.38460 (13)	−0.1378 (2)	0.5819 (6)	0.0293 (9)
C7	0.34103 (14)	−0.1213 (2)	0.6295 (6)	0.0349 (10)
H7A	0.3202	−0.1569	0.6557	0.042*
C8	0.40022 (15)	−0.2145 (2)	0.5758 (6)	0.0366 (10)
C9	0.46214 (15)	−0.0985 (2)	0.4738 (7)	0.0392 (11)
C10	0.46025 (15)	0.2587 (2)	0.5131 (7)	0.0428 (11)
H10A	0.4762	0.2170	0.4895	0.051*
C11	0.44556 (13)	0.3720 (2)	0.5500 (6)	0.0327 (10)
C12	0.40613 (13)	0.3312 (2)	0.5766 (6)	0.0327 (9)
C13	0.36540 (13)	0.3643 (2)	0.6177 (6)	0.0327 (10)
H13A	0.3396	0.3367	0.6393	0.039*
C14	0.36314 (13)	0.4380 (2)	0.6266 (6)	0.0321 (10)
C15	0.40400 (14)	0.47992 (19)	0.5986 (6)	0.0314 (9)
C16	0.44451 (14)	0.4463 (2)	0.5622 (6)	0.0352 (10)
H16A	0.4711	0.4732	0.5458	0.042*
C17	0.40890 (16)	0.5620 (2)	0.5952 (6)	0.0395 (11)
C18	0.31614 (14)	0.4648 (2)	0.6704 (6)	0.0399 (11)
O1W	0.2366 (4)	0.1989 (7)	0.851 (2)	0.126 (5)	0.38
H1C	0.2379	0.2042	0.9681	0.151*	0.38
H1D	0.2255	0.1565	0.8423	0.151*	0.38
O2W	0.2352 (4)	0.2876 (6)	0.5630 (19)	0.108 (4)	0.38
H2C	0.2495	0.3257	0.6052	0.129*	0.38
H2D	0.2530	0.2509	0.5812	0.129*	0.38
O3W	0.2637 (6)	0.2800 (10)	0.809 (3)	0.110 (6)	0.25
H3C	0.2702	0.3223	0.7767	0.131*	0.25
H3D	0.2564	0.2647	0.9111	0.131*	0.25

	U11	U22	U33	U12	U13	U23
Ag1	0.0433 (2)	0.02077 (18)	0.0675 (3)	−0.00497 (15)	0.01755 (17)	0.00033 (16)
O1	0.0401 (18)	0.0188 (16)	0.126 (3)	−0.0020 (13)	0.0233 (19)	0.0014 (17)
O2	0.0414 (18)	0.0328 (18)	0.096 (3)	0.0092 (14)	0.0283 (17)	0.0062 (17)
O3	0.0345 (16)	0.059 (2)	0.051 (2)	−0.0025 (14)	0.0147 (15)	−0.0074 (16)
O4	0.0297 (16)	0.064 (2)	0.054 (2)	−0.0008 (15)	0.0076 (15)	0.0002 (16)
O5	0.0422 (18)	0.0341 (19)	0.093 (3)	0.0100 (14)	0.0259 (18)	−0.0047 (17)
O6	0.0364 (17)	0.0408 (19)	0.104 (3)	−0.0013 (15)	0.0317 (18)	−0.0021 (18)
O7	0.0478 (19)	0.0226 (16)	0.096 (3)	0.0029 (14)	0.0256 (19)	0.0006 (16)
O8	0.049 (2)	0.0314 (19)	0.110 (3)	−0.0119 (15)	0.032 (2)	−0.0032 (18)
N1	0.0261 (18)	0.0219 (17)	0.047 (2)	−0.0002 (14)	0.0087 (15)	−0.0005 (15)
N2	0.0201 (16)	0.033 (2)	0.051 (2)	−0.0036 (14)	0.0140 (15)	−0.0005 (16)
N3	0.0298 (18)	0.0201 (18)	0.068 (3)	0.0007 (14)	0.0167 (17)	0.0010 (16)
N4	0.0279 (18)	0.030 (2)	0.066 (3)	0.0014 (15)	0.0215 (17)	0.0003 (17)
C1	0.028 (2)	0.028 (2)	0.051 (3)	0.0021 (18)	0.008 (2)	−0.0022 (19)
C2	0.0202 (19)	0.028 (2)	0.039 (3)	−0.0009 (16)	0.0099 (17)	−0.0025 (18)
C3	0.0240 (19)	0.022 (2)	0.037 (2)	−0.0045 (16)	0.0071 (17)	0.0005 (17)
C4	0.0220 (19)	0.024 (2)	0.042 (3)	−0.0034 (16)	0.0110 (18)	0.0015 (17)
C5	0.024 (2)	0.030 (2)	0.037 (3)	−0.0024 (17)	0.0052 (17)	0.0002 (18)
C6	0.031 (2)	0.0189 (19)	0.038 (3)	−0.0007 (16)	0.0056 (19)	0.0010 (17)
C7	0.032 (2)	0.026 (2)	0.049 (3)	−0.0042 (18)	0.012 (2)	0.0023 (19)
C8	0.035 (2)	0.027 (2)	0.052 (3)	0.0037 (19)	0.017 (2)	−0.0011 (19)
C9	0.034 (2)	0.029 (2)	0.057 (3)	0.0048 (19)	0.013 (2)	−0.001 (2)
C10	0.038 (2)	0.026 (2)	0.068 (3)	0.0064 (19)	0.018 (2)	−0.001 (2)
C11	0.028 (2)	0.025 (2)	0.047 (3)	−0.0020 (17)	0.0123 (19)	0.0020 (18)
C12	0.033 (2)	0.022 (2)	0.045 (3)	0.0006 (18)	0.0105 (18)	0.0026 (19)
C13	0.028 (2)	0.024 (2)	0.049 (3)	−0.0010 (17)	0.0154 (19)	0.0035 (18)
C14	0.028 (2)	0.028 (2)	0.042 (3)	0.0061 (17)	0.0098 (18)	−0.0003 (18)
C15	0.033 (2)	0.021 (2)	0.042 (3)	−0.0025 (17)	0.0095 (19)	0.0004 (17)
C16	0.029 (2)	0.026 (2)	0.052 (3)	−0.0052 (17)	0.013 (2)	0.0035 (19)
C17	0.045 (3)	0.029 (2)	0.045 (3)	−0.003 (2)	0.011 (2)	−0.001 (2)
C18	0.031 (2)	0.035 (3)	0.055 (3)	0.001 (2)	0.011 (2)	0.000 (2)
O1W	0.100 (7)	0.111 (7)	0.168 (9)	0.017 (6)	0.025 (7)	−0.013 (7)
O2W	0.096 (7)	0.071 (6)	0.158 (9)	−0.017 (6)	0.025 (6)	0.000 (6)
O3W	0.095 (9)	0.102 (9)	0.142 (10)	−0.019 (7)	0.050 (8)	0.029 (8)

Ag1—N3	2.100 (3)	C2—C3	1.393 (5)
Ag1—N1	2.108 (3)	C3—C4	1.393 (5)
O1—C8	1.307 (5)	C4—C5	1.369 (5)
O1—H1	0.8498	C4—H4B	0.9300
O2—C8	1.205 (5)	C5—C6	1.415 (5)
O3—C9	1.254 (5)	C5—C9	1.503 (5)
O3—H3	0.8499	C6—C7	1.374 (5)
O4—C9	1.267 (5)	C6—C8	1.500 (5)
O4—H4	0.8500	C7—H7A	0.9300
O5—C18	1.280 (5)	C10—H10A	0.9300
O6—C18	1.242 (5)	C11—C16	1.388 (5)
O7—C17	1.277 (5)	C11—C12	1.394 (5)
O7—H7	0.8499	C12—C13	1.387 (5)
O8—C17	1.215 (5)	C13—C14	1.378 (5)
N1—C1	1.329 (5)	C13—H13A	0.9300
N1—C3	1.385 (5)	C14—C15	1.442 (5)
N2—C1	1.328 (5)	C14—C18	1.508 (5)
N2—C2	1.380 (4)	C15—C16	1.375 (5)
N2—H2A	0.8600	C15—C17	1.536 (5)
N3—C10	1.322 (5)	C16—H16A	0.9300
N3—C12	1.391 (5)	O1W—H1C	0.8500
N4—C10	1.339 (5)	O1W—H1D	0.8501
N4—C11	1.370 (5)	O2W—H2C	0.8501
N4—H4A	0.8600	O2W—H2D	0.8501
C1—H1A	0.9300	O3W—H3C	0.8496
C2—C7	1.391 (5)	O3W—H3D	0.8496
N3—Ag1—N1	173.32 (12)	C2—C7—H7A	121.3
C8—O1—H1	120.1	O2—C8—O1	124.2 (4)
C9—O3—H3	109.5	O2—C8—C6	122.9 (4)
C9—O4—H4	115.8	O1—C8—C6	112.9 (3)
C17—O7—H7	114.2	O3—C9—O4	121.2 (4)
C1—N1—C3	104.7 (3)	O3—C9—C5	117.2 (4)
C1—N1—Ag1	132.6 (3)	O4—C9—C5	121.4 (4)
C3—N1—Ag1	122.6 (2)	N3—C10—N4	113.2 (3)
C1—N2—C2	107.4 (3)	N3—C10—H10A	123.4
C1—N2—H2A	126.3	N4—C10—H10A	123.4
C2—N2—H2A	126.3	N4—C11—C16	133.1 (4)
C10—N3—C12	105.0 (3)	N4—C11—C12	106.3 (3)
C10—N3—Ag1	126.3 (3)	C16—C11—C12	120.6 (3)
C12—N3—Ag1	128.6 (2)	C13—C12—N3	131.1 (3)
C10—N4—C11	107.0 (3)	C13—C12—C11	120.4 (4)
C10—N4—H4A	126.5	N3—C12—C11	108.5 (3)
C11—N4—H4A	126.5	C14—C13—C12	120.0 (4)
N2—C1—N1	113.2 (3)	C14—C13—H13A	120.0
N2—C1—H1A	123.4	C12—C13—H13A	120.0
N1—C1—H1A	123.4	C13—C14—C15	119.3 (3)
N2—C2—C7	132.6 (3)	C13—C14—C18	112.9 (3)
N2—C2—C3	105.5 (3)	C15—C14—C18	127.8 (4)
C7—C2—C3	121.9 (3)	C16—C15—C14	120.0 (4)
N1—C3—C2	109.3 (3)	C16—C15—C17	111.7 (3)
N1—C3—C4	130.2 (3)	C14—C15—C17	128.2 (3)
C2—C3—C4	120.5 (3)	C15—C16—C11	119.6 (3)
C5—C4—C3	117.8 (3)	C15—C16—H16A	120.2
C5—C4—H4B	121.1	C11—C16—H16A	120.2
C3—C4—H4B	121.1	O8—C17—O7	121.2 (4)
C4—C5—C6	121.5 (3)	O8—C17—C15	119.1 (4)
C4—C5—C9	115.5 (3)	O7—C17—C15	119.7 (4)
C6—C5—C9	122.9 (3)	O6—C18—O5	119.8 (4)
C7—C6—C5	120.9 (3)	O6—C18—C14	118.7 (4)
C7—C6—C8	120.3 (3)	O5—C18—C14	121.5 (4)
C5—C6—C8	118.8 (3)	H1C—O1W—H1D	97.8
C6—C7—C2	117.3 (3)	H2C—O2W—H2D	112.1
C6—C7—H7A	121.3	H3C—O3W—H3D	130.0

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O7i	0.85	1.77	2.603 (4)	168
O3—H3···O3ii	0.85	1.71	2.528 (5)	162
O4—H4···O4iii	0.85	1.66	2.500 (6)	168
O7—H7···O5	0.85	1.54	2.389 (4)	176
N2—H2A···O6iv	0.86	1.88	2.733 (4)	173
N4—H4A···O8v	0.86	2.04	2.805 (4)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O7i	0.85	1.77	2.603 (4)	168
O3—H3⋯O3ii	0.85	1.71	2.528 (5)	162
O4—H4⋯O4iii	0.85	1.66	2.500 (6)	168
O7—H7⋯O5	0.85	1.54	2.389 (4)	176
N2—H2A⋯O6iv	0.86	1.88	2.733 (4)	173
N4—H4A⋯O8v	0.86	2.04	2.805 (4)	148

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .